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Merck

318426

Sigma-Aldrich

3,3′-Dihexyloxacarbocyaniniodid

98%

Synonym(e):

3-Hexyl-2-[3-(3-hexyl-2(3H)benzoxazolyliden)-1-propenyl]-benzoxazoliumiodid

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About This Item

Empirische Formel (Hill-System):
C29H37IN2O2
CAS-Nummer:
Molekulargewicht:
572.52
Beilstein:
9312562
MDL-Nummer:
UNSPSC-Code:
12171500
PubChem Substanz-ID:
NACRES:
NA.47

Qualitätsniveau

Assay

98%

Form

powder or chunks

Methode(n)

titration: suitable

mp (Schmelzpunkt)

219-221 °C (lit.)

Löslichkeit

chloroform: 25 mg/mL, clear to slightly hazy, orange

λmax

485 nm

ε (Extinktionskoeffizient)

≥120000 at 483-488 nm in methanol at 0.01 g/L

Fluoreszenz

λex 485 nm; λem 501 nm in methanol

Anwendung(en)

diagnostic assay manufacturing
hematology
histology

Lagertemp.

room temp

SMILES String

[I-].CCCCCCN1\C(Oc2ccccc12)=C\C=C\c3oc4ccccc4[n+]3CCCCCC

InChI

1S/C29H37N2O2.HI/c1-3-5-7-13-22-30-24-16-9-11-18-26(24)32-28(30)20-15-21-29-31(23-14-8-6-4-2)25-17-10-12-19-27(25)33-29;/h9-12,15-21H,3-8,13-14,22-23H2,1-2H3;1H/q+1;/p-1

InChIKey

XVLXYDXJEKLXHN-UHFFFAOYSA-M

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Allgemeine Beschreibung

3,3′-dihexyloxacarbocyanine iodide (DiOC6) is a supravital lipophilic fluorochrome. This cationic dye is employed to stain mitochondria and endoplasmic reticulum in animal and plant cells. In addition, it acts as a very rapid, consistent and highly selective fluorochrome for endophytic ascomycetes in plant roots and liverworts. DiOC6 also facilitates the detection of different mitochondrial changes happening during early apoptosis.

Anwendung

3,3′-Dihexyloxacarbocyanine iodide has been used:
  • to selectively stain endophytic ascomycetes in plant roots and liverworts
  • to visualize thrombus formation and platelet aggregate
  • to visualize forchlorfenuron (FCF)-induced changes in mitochondrial morphology

Piktogramme

Exclamation mark

Signalwort

Warning

Gefahreneinstufungen

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Zielorgane

Respiratory system

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

dust mask type N95 (US), Eyeshields, Gloves


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Microfluidic cell sorting: Towards improved biocompatibility of extracorporeal lung assist devices
Bleilevens C, et al.
Scientific reports, 8(1), 8031-8031 (2018)
Examination of living and fixed gametes and early embryos stained with supravital fluorochromes (Hoechst 33342 and 3, 3?-dihexyloxacarbocyanine iodide)
Luttmer SJ and Longo FJ
Gamete Research, 15(3), 267-283 (1986)
Ashlesha A Kadam et al.
Biochimica et biophysica acta, 1861(1 Pt A), 2942-2955 (2016-10-23)
Apoptosis Inducing Factor (AIF), a phylogenetically conserved mitochondrial inter-membrane space flavoprotein has an important role in caspase independent cell death. Nevertheless, AIF is also essential for cell survival. It is required for mitochondrial organization and energy metabolism. Upon apoptotic stimulation
Xueying Zhuang et al.
Mycological research, 113(Pt 4), 417-431 (2008-12-31)
Growth and organelle morphology in the wood rotting basidiomycete fungus Phanerochaete velutina were examined in Petri dishes, on agar-coated slides, and in submerged cultures, using DIC, fluorescence and four-dimensional (4-D; x,y,z,t) confocal microscopy, with several fluorescent probes. Phanerochaete is ideal
Yanyan Zheng et al.
European journal of medicinal chemistry, 125, 902-913 (2016-10-22)
Emodin, a natural anthraquinone derivative isolated from Rheum palmatum L., has been demonstrated to exhibit good anti-cancer effect. In this study, a series of novel quaternary ammonium salts of emodin, anthraquinone and anthrone were synthesized and their anticancer activities were

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